


Trust Me

by Id_flyifihad_wings



Series: Prompts, Drabbles, and 5-Min Writings (Plus Other Things) [4]
Category: Supernatural
Genre: Bottom Dean, Dean hates rough sex, F/M, M/M, Past Abuse, Plot What Plot/Porn Without Plot, past trauma
Language: English
Status: Completed
Published: 2016-08-20
Updated: 2016-08-20
Packaged: 2018-08-09 21:01:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,770
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7817083
Author URL: https://archiveofourown.org/users/Id_flyifihad_wings/pseuds/Id_flyifihad_wings
Summary: <blockquote class="userstuff">
              <p>Over the course of Dean's four years in college, he tries to strike up a relationship with someone. Things don't turn out the way he expected. </p><p> </p><p>Or in which Dean just really wants someone gentle to have sex with.</p>
            </blockquote>





	Trust Me

The first time, Dean led a girl back to his dorm room and she took control once inside. Dean wasn't used to his girlfriends being so rough, but she insisted on topping. Of course, that meant Dean was lying on his back doing zero work (his arms tied above his head) while she grinded down onto his dick. If he tried moving at all she would slap him and tell him to be a "good bottom." She was warm, and very wet. She also was adamant that Dean not wear a condom.

Lisa was on birth control after all. She said she wouldn't get pregnant. She was very physical with her "affection." 

"Are you sure about this, Lis?" Dean wondered as she began to move. 

"Oh, Dean. Just trust me, baby. I'll make it so good." 

She leaned over him and dug her nails into his chest, her rough movements were enough to send Dean's cock into danger mode. She didn't stop her ministrations until she had achieved orgasm. 

Her pulsing pussy sent Dean over the edge, despite how utterly not turned on he was. She left him with a bleeding chest and sore arms. His dick even twitched uncomfortably in his boxers as he dressed. He made sure to clean the streaks of blood from his chest before pulling his shirt back over his head. Dean broke up with her later that night. 

\-----

The second time it was a boy he didn't know well. Aaron seemed to like him well enough, and they had made quick work of an easy friendship. "Trust me." But now, he was being shoved against the wall while bruises were sucked into his skin. 

Aaron rutted against his leg shamelessly, seeking friction any way he could. "Oh, God, Dean. I want you to fuck me so hard. So good, you taste so good." 

Dean had no idea what to do with that information. Aaron seemed to know that he was inexperienced, and took the lead. His fingers slicked up at Dean's hole made him regret this entire decision. It was uncomfortable at the brutal pace Aaron set. Even hitting his prostrate wasn't enough to send Dean into fits of pleasure. 

When Aaron finally lubed up his cock and rolled a condom into place, Dean had grown so nervous he wasn't sure he was prepared. The pressure at his hole was intense as he was filled with Aaron's dick. 

"Fuck, you feel good. So tight," Aaron whined happily. He bottomed out so quickly that Dean's eyes teared up. Aaron wasn't a small man, he was surprisingly well endowed for as scrawny as he was. He hardly waited for Dean to adjust before he was carelessly thrusting into him harshly. 

Dean tried to make him slow down, but he couldn't get any words out. He was too busy trying not to cry out in pain. He wasn't lubricated enough, and the burning was beginning to be too much for Dean. His ass was starting to ache already. 

"So good, Dean," Aaron moaned. He called his name like it was a prayer. Dean dropped his head to the pillow and cried out as hurt spiraled through him while Aaron's pace sped up. His thrusts were rough and hurried. Aaron took this as pleasure and quickened his already speedy thrusts. 

"Fuck!" Dean couldn't hold back the agonized yell as Aaron stretched him wide and rode him hard. He could feel his body draping his, Aaron's breath hot on his neck. Dean was crying for a different reason as Aaron bit into the tender skin at his shoulder, his cock twitching in orgasm. Dean could feel the warmth, though the condom caught any sperm that may have flowed through him. 

Aaron left soon after that, telling Dean to call him again some time. Dean threw his number away and went to take care of his bleeding shoulder and painfully unattended dick. The hickeys at his neck made him wince as memories of bruised skin flooded his mind. "Fuck, Dean. Fuck," he griped at himself as he looked away. He covered them up. 

\-----

The third time, Dean managed to find a nice guy for grabs. Benny and himself had grown a strong bond over the last few months. "Just trust me," Benny had told him. 

Of course, Benny wasn't much for vanilla sex. He handcuffed Dean to the bed and forced him to the edge countless times, not allowing him to cum. And, fuck, he hated it. It wasn't until Benny brought out something called a cock ring and stuck it on Dean that he began to understand. 

He undid the handcuffs and forced Dean to his knees in front of him. Dean grunted as his legs made impact with the ground. Benny roughly fucked Dean's mouth, making his jaw ache as he tried to take it. Dots spotted his vision as he found it hard to breathe. He was forced to swallow all of Benny's ejaculate and when the man pulled out, Dean backed away, crying silently. 

"I can't do this. No. Get me out and leave, please," Dean begged sadly, fighting to keep the waver from his voice. His lip trembled though, and Benny was immediately soothing him and helping him stand. He cleaned his chin and gave him a short massage to stretch out his shoulders before Dean forced him out the door. 

"Don't come back," Dean ordered with a watery tone. Benny apologized once, nearly cut off as Dean slammed the door in his face. Only when he was sure Benny was gone did he allow himself to full out sob. He deleted Benny's number and refused to look at the bruises on his knees in case the memories came back. 

\-----

The fourth time, Dean figured he'd give the guy a chance. They knew each other well enough. Dean had even entrusted him with his past. He was nice, and his eyes were enough to get Dean lost. Blue, like oceans. His mussed up hair was dark and thick, and made Dean want to run his hands through it. His body had healed by then. 

When they reached Dean's room, Cas simply started out by sitting on Dean's bed and getting comfortable in the room. "You have an eccentric taste in music," he pointed out. Dean glanced at the posters of classic rock bands in his wall. No one else had noticed them. "Though, I quite like Led Zeppelin," Castiel admitted. 

"They're a great band," Dean agreed, sitting by the odd boy on his bed. 

It was only when Dean sat down that Cas leaned forward and gave him a gentle kiss. Dean was surprised. Cas scooted closer to him and they were kissing again. Castiel's hand came up to cup Dean's jaw. He was unhurried. Their tongues mingled and Dean could taste the toothpaste Cas had used earlier to brush his teeth. It was slightly spicy, like cinnamon. 

Cas's hands moved to the hem of Dean's tee, pulling it over his head and making sure to drag his fingers over every inch of skin he could reach. Dean blushed unexpectedly at the contact and found himself embarrassed when Cas moved back to discard his own shirt too, finding a well-cut torso. He felt suddenly self-conscious. 

Cas seemed to notice this as he gently guided Dean to lay down and trailed soft kisses down to his stomach. "So beautiful," he murmured as he went. His hands roamed over Dean's broad chest, thumbs gliding over already hardening nipples. That earned a soft moan from Dean. 

Without a second thought, Cas came back to suck and lathe at Dean's buds, teasing them until Dean was practically writhing underneath him. "So reactive, Dean. Perfect," Cas praised as he rose to meet Dean's lips in a heated kiss. Dean wasn't sure what to do with his hands, he'd never had free range of motion before. Cas reached down and twined their fingers together, moving to mouth at Dean's jaw and neck. 

Fear coursed through him and he ripped his hands out of Cas's grip to push him away. "Wait!" he cried nervously. Cas didn't look put out, he simply nodded and allowed Dean his moment. "Don't. I don't want bruises," he pleaded helplessly. 

Cas looked shocked and gave a bitter laugh. "Dean," he sounded upset. "After you told me your past, you expect me to leave a mark on you?" he asked sadly, looking hurt. "I don't ever want to see you hurt again, and I would never bruise you," he leaned in to lay a chaste kiss to Dean's forehead. 

"Ok. Ok," Dean nodded and Cas linked their hands once again. He bent down and kissed Dean's throat again, sighing happily as he slowly made his way down to his chest, his stomach, hands sliding away from hands to unbuckle Dean's belt and work his jeans open. Dean's breathing sped up nervously, and Cas abandoned the job to return his attention to Dean's mouth. 

"You're gorgeous, Dean, I hope you know that," Cas said between kisses. Dean could barely hold back his sob at the words. Cas again returned to his jeans, leaning down to plant kisses on Dean's stomach as he pushed down the denim. Thankfully they had both already taken off their shoes before. 

Cas threw the jeans to the ground and took Dean's hand again, pulling him up to him. Their mouths met once more. Cas's hands reached to guide Dean's own to his jeans, letting him take over once the message was across. They were soon in only boxers, and Dean was actually surprised to find he was hard with arousal. 

"Do you trust me, Dean?" Cas asked gently, sending Dean back to all the times he'd been wronged. Yes, they were having sex. But it was different than the other times, somehow. 

"Yes," replied Dean finally, nodding his head as Cas reached down and started taking off his boxers. 

"Oh," he suddenly murmured, looking put out. "I forgot lubricant," he told Dean. That made the green-eyed boy laugh, while Cas stood (buck naked) and left the room. 

"You forgot clothes, too!" Dean called after him. He should probably invest in a bottle of lube if he planned on keeping Castiel any longer. So far, he could see the strange boy in his future. Cas bounded back into the room with red cheeks and a half-empty bottle of lube, and leaned against the door for a moment. 

"Thankfully no one was in the hallway," he mumbled as he came back to the bed. Dean gulped slightly when he finally took the time to check out Cas's dick. Not only was it wide enough to wound someone, it was also long. Bigger than Aaron, and Dean painfully remembered that experience. Cas set the lube down and motioned for Dean to take off his underwear, to which he happily obliged. 

Once the garment was thrown on the floor, Cas bent down to softly lick up his length. "Fuck," Dean exclaimed, throwing his head back and squeezing his eyes shut. 

"Is that a good fuck, or a bad one?" wondered Cas while absently stroking Dean's cock. 

"Good, definitely good," Dean managed to get out. Cas gave a grin and sat back on his legs, reaching for the bottle. Dean started to turn onto his back but Cas stopped him. 

"I want to see your eyes, Dean Winchester," he told him, giving a gentle slap to Dean's thigh. Continuing to lube his fingers, Cas finally set the bottle aside and went to work. One finger played at Dean's tight ring of muscle, pushing at the entrance slowly until it slipped inside. Dean shifted slightly as the discomfort set in, but Cas moved slow and seemed to search for something inside. 

A breathy moan broke from Dean's mouth when Castiel found his prostrate, and he gave a triumphant smile. His finger brushed against that sweet spot each time, sending Dean into a wriggling mess once again. He pressed a second digit inside and went on with his ministrations. 

Once Dean was used to that, he slipped yet another finger inside. Dean grimaced at the sensation, but stuck with it as the burn slowly subsided. Cas slowly began to scissor Dean open, knowing he wasn't use to any of this. 

After a few minutes, he pulled his fingers out and turned to his own cock. He gave it a few short strokes to get it fully erect, slipped on a condom, and lubed it up profusely. He noticed Dean was watching intently, and shot him a wink. "This will be easier for you if you relax, Dean. Don't focus on anything but breathing," he suggested. 

He waited until Dean nodded before positioning himself at his opening. Dean groaned when he started pressing inside, but Cas stopped and gave him a bit of time. He grabbed at Dean's legs and raised them up to rest over his shoulders. Dean shot him an odd look. "Breathe," Cas ordered quietly. Deep breaths followed his voice, and Cas started pushing in again. When the muscles in Dean's legs tightened up, he stopped and told Dean once more to relax. 

Castiel was over halfway in when Dean gave a quivering breath that made him hesitate. "Am I hurting you?" he asked with worry. Dean shook his head, refusing to meet his gaze. "Are you doing well, Dean?" 

"I'm good," Dean mumbled, eyes still closed. "It's good," he added as an afterthought, voice soft and unsure. Cas hummed and continued, leaning over Dean's body and pressing his legs closer to his chest. He bottomed out, and Dean's hand absentmindedly reached down to stroke himself. 

Cas closed his eyes and focused on giving time to adjust instead of pounding into him. He wanted to make this good for both of them. "You can move now, Cas. I think I'm good," Dean spoke up and interrupted his train of thought. With a nod, Cas pulled out and started into gentle thrusts. 

Fuck, Dean didn't think this could feel so good. A practiced hand joined his own to help him, making him moan at the feeling. With the full sensation of Cas moving inside him and his hand at his cock, Dean could feel his orgasm building by the heat pooling in his stomach. "Fuck, Cas, I'm gonna-" he was cut off by a groan of pleasure as Cas sped up his thrusts and dropped his head to his chest. 

"Me too," he finally replied, voice ragged and weary. Dean's legs had fallen from Cas's shoulders a few minutes ago, and now they rose up to twist around Cas's hips and help him get deeper inside. Dean was soon a moaning mess, green eyes closed and hand stilled, so Cas took up the job. 

They were soon kissing again, tongues gliding hotly across the other's. Cas captured Dean's moans in his mouth, breathed in his minty taste. He realized his hips were beginning to stutter in their rhythm and Dean's eyes were only half-open as he panted his joy. "Open your eyes, Dean. I want to see them," Cas commanded with fatigue in his voice. 

Dean did as he was told, apple green disappearing with his lust-filled pupils. Cas gave a final thrust, a low groan breaking from his mouth as he released his load. That sent Dean over the edge, and he gave a high, keening moan that had his face going red and Cas laughing kindly, even as Dean cummed over his stomach and chest. 

Cas pulled out slowly, removed his condom, tied it off before flinging it into the trashcan at Dean's door. He nearly missed. Dean was about to stand to clean himself, when Cas bent to lick up every strip of cum on his skin. "How was that for you, Dean?" he asked when he finished. 

"Uh-" Dean worked his mouth to find what to say, his face still flushed with embarrassment and exertion. "I'm gonna be sore tomorrow," he mumbled, watching Cas lap at his stomach with interest. 

"That doesn't mean it necessarily felt good," Cas reprimanded him teasingly. 

"I - it was good. Better than good," Dean finally spat out, rubbing at the back of his neck. Cas met his eyes and smiled happily, his eyes bright as he leaned up and tenderly kissed him. 

Dean put in a heart emoji next to Cas's name on his phone, and even snapped a naked picture of him for later fantasies. He decidedly kept the wild-haired, ocean-eyed man close the rest of the year. And when they graduated, they rented a small apartment in Michigan together.


End file.
